


The Valentine's Day Proposal

by ForTheLoveOfChuck



Category: Supernatural
Genre: Fluff, M/M, Smut, Valentine's Day
Language: English
Status: Completed
Published: 2015-02-11
Updated: 2015-02-15
Packaged: 2018-03-11 21:13:05
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 2,836
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3333050
Author URL: https://archiveofourown.org/users/ForTheLoveOfChuck/pseuds/ForTheLoveOfChuck
Summary: <blockquote class="userstuff">
              <p>Just a little piece I wrote about the boys getting together for Valentine's day and beyond.</p>
            </blockquote>





	1. Getting over the Fear

**Author's Note:**

> This is my first true fan fiction piece so I am very sorry if it isn't great. Leave your comments and suggestions in the box..

“Hey Dean…” Sam whispers while he pulls himself back up the passenger seat.

“What’s up, Sammy?” Dean asks offhandedly

“I need to stop” Sam tells his brother hoping he gets the hint.

“Stop what? Oh… you drank too much coffee this morning? Every time Sam... Alright, There is a rest area just up the road. About 15 minutes, think you’ll make it to then?” Dean says toyingly

“Thanks.” Sam says in return

 

The boys then sit in uncomfortable silence while Dean debates talking.

 

“So, uhhh, Sam. Today is February 10th. Think we can finish this case before Valentine’s day?” Dean asks awkwardly about 10 minutes later.

“Depends on how many of the demons are there, but I figure so… Why?” Sam asks timidly

“Cool, cool. No reason.”

Another 5 minutes and they have reached the rest area. Sam rushes out and quickly dashes to the bathroom.

About 3 minutes later Sam comes back and Dean takes an opportunity to make a jab at sam.

“You sure rushed out of here quick, maybe you should hold back on the coffee for a while. Give your bladder a break.” Dean wittily tells Sam.

“Whatever, Jerk.” Sam quips back.

“Bitch………………………………………..Hey, uhh, you think maybe you’ll find a girl for Valentine’s day?” Dean awkwardly asks as he scratches the back of his neck absent mindedly.

“Nah, Probably just stay in the motel room. Maybe pick up some beer. But you can go out if you like, I’m sure the town will have a bar somewhere.”

“Yeah, Maybe.”

Another long stent of awkward silence now commences. but by now the pair have reached the motel.

“Actually, probably not.” Dean says awkward but firm. And he steps out of the Impala

“Who are you, and what have you done with my brother?” Sam asks across the roof of the car.

“What do you mean?” Dean says quizzically.

“Nothin, Dean. It’s just I've never heard you say you didn't want to go to a bar and pick up a girl.” Sam says in a confused voice.

“I dunno man, I think maybe this year I just wanna spend the stupid day with you. Ya know, stay in. Grab a couple beers. Rent Casa Erotica on Pay per view.”

“Why the hell would we rent Casa Erotica Dean?” Sam says with a good amount of confusion.

“Oh, that’s right, Gabriel. Ruined that one, didn't you, you bastard?!?” Dean yells in a raised voice toward heaven. “We could rent something else.” he suggests.

“What is your problem, Dean? We never spend Valentine’s together. Why are you acting so weird?” Sam asks quizzically and a little annoyed while he opens their room. 

“Nothing. Okay, Nothing. Just leave it. What do you want to eat for dinner, Sam?” Dean says a little ruder than necessary.

“Whatever, lets find a diner and research this case” Sam answers; obviously hurt while he skulks out the door. 

“Wait, Sammy, It’s just…… I don’t do this kinda thing…..” Dean yells after his brother.

“Fine, Come out here and tell me what the problem is then.” Sam snaps back.

Dean decides to oblige and follows Sam to the Impala. “Sam…. you gotta understand… I’m not……. Wow…. I’m umm… not good at this….” Dean finally stutters through.

“Not good at what Dean?” Sam exclaims up at Dean, “Telling me your feelings? Because, trust me, I know! I never know whether you are sick, horny, in love, or anything. And it drives me fucking insane.”

“Fine then Sam, I’ll tell you, Yes.” Dean yells out gruffly.

“Yes?” Sam asks, incredulous.

“Yes. Yes, Sam, I am all of those things; because of you. I get into the Impala and feel like I will go mad. So when I asked if you were going to find a girl for Valentine’s day I was really glad when you said no. I was TRYING to do and say what you like Sammy. I was trying to find a way to ask you this without blowing the ‘no chick-flick moments’ rule” Dean bellows from the balcony to Sam who is now leaned against the passenger side.

“Ask me what?” Sam unashamedly asks as he walks back up the steps to their door.

“Ask you to be my ‘Valentine’ or whatever you want to call it..” Dean stammers through when Sam is once again standing in front of him

“I thought you would never actually ask.” Sam says with a smile before he leans down and kisses his brother. But is disappointed when his older brother pulls away.

“Oh no, don’t give me the puppy dog eyes. If we’re going to do this, we’re going to do it right. We are going to dinner. And then, maybe I’ll let you kiss me, if I still like you enough” Dean says a little firmer and with a wink.


	2. Awkward First Dates

**Summary for the Chapter:**

> A diner. same side booth sitting. and kisses. little bit suggestive at the end of what is in store for next chapter

**Notes for the Chapter:**

> Sorry it seems so awkwardly phrased... I am not very good at this... Yes, I do use the verb of "face battling" whoops. it kinda just happened. Super short. but yeah..

“Can’t I just kiss you now? We can still go get dinner.” Sam practically begs.

“Wow, if I’d known you’d react like this I would have asked you out earlier.” Dean says with a grin.

“Shut up." Sam tells Dean playfully.

"Alright, let's go get some food. I'm withering away up here!" Dean says as he playfully shoves his brother in the direction of the Impala.

They find a diner 4 miles from their motel called Lil’ Sally’s where as soon as they are at their booth Sam makes another move.

“Dean, can I sit on that side?” Sam asks in a innocent voice

“Sure, just a sec. let me put my stuff on the other side.” Dean says through the mouthful of crackers he stuffed in his mouth.

“No Dean, I meant WITH you.” Sam says with a nervous chuff.

“Why, there’s more room if we are on opposite sides.”

“Dean…”

“What Sammy? Just cause you’re my Valentine doesn’t mean that we sit on the same side of the booth at the diner.” Dean answers a little gruffly.

“Fine, but I don’t understand what the issue is.” Sam says looking angry, “Nobody knows we’re brothers here Dean.” Sam whispers to avoid drawing attention.

“Fine…………... get over here. And stop being a pouty baby. Life isn’t a box of chocolates and an overstuffed teddy bear.” Dean says sarcastically.

Sam cuddles up next to Dean who is uncomfortable at first, but eventually eases up to put his arm around Sam’s back.

“we’ll take a Side-Spinner Salad combo, extra croutons, and the biggest Cheeseburger you can make. extra onions! Oh, and two beers please.” Dean orders for his brother and then himself. Like usual.

“Why extra onions, Dean? I thought I would get to kiss you later.” Sam asks Dean wistfully.

“Oh, right, well hopefully you won’t mind too much?” Dean taunts with a cheeky grin.

“It’s a good thing we’ve known each other for forever or else I’d have moved back to the other side of the booth by now.” Sam chides back sarcastically.

“I can get them to take the onions off if you want me to, it isn’t an issue Sam.” Dean says, suddenly serious.

“No it’s fine, I don’t really mind. Anyone else and I might. But I have lived and worked with you for 3 something years; I think I’ll survive an onion-y kiss.”

“I didn’t say for sure that I would kiss you yet, little brother.” But then Dean leans across and gives sam a peck on the forehead.

“What was that for? I thought I had to wait for later!” Sam asks only half serious.

“Oh, right. Well, that wasn’t even a real kiss. A real one would be like this.” Dean says defiantly and then leans forward again to plant a deep kiss to Sam’s lips. “You’re sure about this, right?” Dean says as he pulls back a little.

“Would I kiss back if I wasn’t?” Sam answers incredulously with a little punch to deans arm.

“True. Alright.” And leans back in.

****  
  
  


* * *

Dean knocks his glass over when the waitress comes by with their food a few minutes later. Sam and Dean both scramble to untangle themselves and wipe up the mess.

 

"Sorry, Sorry. We didn't mean..... Shit" Sam says watching the golden liquid spill into Dean's lap.

 

"I..I...I'll be back in just a second with a rag for you to wipe up with.." The waitress rushes off and you can hear laughter from the kitchen.

 

"Maybe we should sit on opposite sides... Sorry, Dean..." Sam says with a sigh as he switches back to his side of the booth. Dean's face is beet red from both embarrassment and the act of face battling Sam. 

 

"It's okay, Sammy. Lets just eat so I can get back and change." And Dean takes a huge bite of his burger. He is making noises like a pig in heat. Sam can feel himself become even more aroused.

 

"Okay.... As long as I can watch." Sam tells Dean with a wink. Dean starts choking and the waitress rushes back out to keep him alive.

 

"You clean this up, I've got him taken care of." Sam says as he gets Dean stood up to do the Heimlich. Sam has Dean okay again in a matter of seconds.

 

"Thanks Sammy, I guess I never expected you to look at me like that. I got a bit 'choked up' "Dean says laughing to himself painfully. (choking does hurt after all) 

 

"Not funny Dean"

 


	3. Dean's First Time

**Summary for the Chapter:**

> Almost sex.But not quite yet  
> Dean's first time with a man. Not Sam's. Sam leads, Dean follows. I really suck at this. Please don't judge too harshly.

**Notes for the Chapter:**

> I really don't know how well this is going to go... Hopefully it isn't a complete failure.

"Well, that was certainly an adventure. You ready to head back to the motel and change now Dean?" Sam says concerned as he and his brother walk back out to the Impala.

 

"Fuck, yes, Sam. I usually drink my beer through my mouth: not my pants." Dean shouts and Sam cannot hold in his laughter.

 

"What's so funny Sam? Jealous that my dick gets more beer than you do?" Sam sobers up a bit when Dean says this.

 

"Alright, Alright. Let's get you back." Sam shoves Dean in the small of his back toward the driver's side door.

 

 

* * *

"You can change in front of me, You always have Dean." Sam says seriously.

 

"Well, yeah, But that was before.  What do we do now?" Dean asks

 

"The same I guess, Dean, I promise to try not to look at your glorious body. There, does that make you happier?" Sam answers; sarcasm thick.

"Not exactly, but whatever." And Dean walks out of the bathroom into the main room. stark Naked.

"Yeah, No way I'm looking away from that, Dean. I'd have to be fucking blind not to realize how hot you are." Sam says while rubbing his crotch with the heel of his hand.

“Sam. Don’t” Dean warns Sam. but it’s too late. the younger brother is already across the room standing right in front of his brother. He looks down into Dean’s beautiful green eyes and Dean can tell he’s already gone. “Since when did my body effect you like this, Sammy?”

“It always has, Dean, I just never figured you felt the same way. So I took a lot of cold showers.” Sam says in a husky voice.

“Sam…..We can’t” Dean looks sadly into Sam’s disappointed eyes.

“Why not? We both want to.” Sam says looking down to where Dean’s privates are standing at attention.

“I know, it’s just, I umm……. I’ve never even been fingered down there….. I’m scared Sam.” Dean tells Sam, who looks back at his brother with a kinder smile.

**  
“You don’t need to worry Dean, It might be your first time. But it isn’t mine.” Sam states, completely serious.**

Dean still Looks very uncomfortable, but when Sam leans in to kiss him he doesn't pull away. 

* * *

"I'll only do this if you feel okay with it, Dean." Sam whispers sincerely into dean's ear.

 

"I'm okay Sam, I want to. I know you'll take care of me." Dean gruffly answers back. 

 

"Okay" Sam says with a smile "you won't regret it"

 

Sam leans back in to a slow, soft kiss which become deeper the more they realize they want this. 

 

"I never would have thought that would feel good, Sammy" Dean wimpers as Sam gives his nipple a tweak under his shirt. 

 

"Told you" Sam taunts as he takes his brothers shirt off to reveal his fit chest and perky nipples. He takes one in his mouth but is soon overtaken with a fit of laughter and lays down on the bed inviting Dean to lay next to him. 

 

"What is so funny?" Dean looks worried.

 

"I...I just remembered that time you told me about when you said your perky nipples made you special. It just.. made me laugh" Sam answers in a fit of giggles. 

 

"Remember that time I went out with dad to the bar and got more girls than he did? Good times, good times."Dean reminisces. But then notices that Sam looks upset. "What's wrong? Was it something I said?"

 

"No.. It's.. nothing." stutters Sam, and leans back over to kiss Dean again.

 

"No it's not 'nothing', it was the girls wasn't it? I didn't mean to... I was trying to make you laugh by making fun of our fathers skills. I didn't mean the girls Sammy, I only want you right now. I want you to fuck me into next week. I want you to finger me until I let go between us. I only want you, Sammy" Dean whispers sincerely. Looking into Sam's hazel eyes he really did feel at home. 

 

"Okay, good." Sam whispers and with a cruel laugh "and I can't wait to make you come so many times the sheet is soaked."

 


	4. Easy come, Easy go

**Summary for the Chapter:**

> They have sex, for real this time. 
> 
> No fluff in this chapter.Just sex, and it is probably hard to follow.. whoops. Hope it isn't too bad. Actually it probably is... It's probably the wrist fanfiction piece you have read.. sorry.

**Notes for the Chapter:**

> I know it's hard to follow... sorry... oh and I removed the 5th chapter. No time, or Wi-Fi.

Chapter 4: easy come, easy go.

"Come on, Sammy, I won't break." Dean whines pleadingly.

"I know you won't break."Sam says back rolling his eyes, "but you've never done this before, and I want it to be good."

"Fine, do what you want." Dean says exasperated while he falls back onto the bed.

"Gonna make it so good for you Dean, wanted to do this for a while." Sam gasps out between kisses.

 

"Don't get me wrong Sammy, the kissing is great. But can we move this along? I feel like I'm going to come already, and we haven't really done anything but kiss for five minutes." Dean persists as he pulls away from his brother.

"Fine, you're a lot more demanding then I expected." Sam says with irritation, and grabs his brother's cock giving it a few pulls before he gets his mouth on it. 

"Damn, best blowjob ever dude! Where did you learn to do that?" Dean gasps out before he lets his resolve give out.

"College." Sam says matter-of-factly before sucking back down to catch the come his brother feeds him.  
"That was quick. Ya ready for the real thing now?"

"Yeah, I'm ready." Dean pants out, and Sam starts to kiss Dean again. 

Sam flips his brother over and remembers he needs lube. Luckily Sam knows where Dean keeps it. He spreads a generous amount on his fingers as he walks back over to the bed. Slowly he circles the rim of dean's hole. Once he feels some of the tension release he slowly inserts his index finger in until he finds dean's prostate. Sam reaches his other hand around to stroke Dean's cock back to full attention. 

"Give me more, Sammy" Dean pleads while he rides his brother's finger. 

Sam adds another finger, and seconds later adds a third. "Fuck it, think you can handle my cock now baby?

"Uh-huh" Dean whimpers out, and cries out a little when Sam slides out of him. 

Sam crosses back to the corner of the room to take his clothes off and slicks his cock up before flipping his brother back over. "Want to see your face Dean, can't wait to see you when you come." Dean whimpers slightly as Sam slowly pushes in. "So tight Dean, fits me perfect." Sam gives his brother a soulful look that asks "are you still okay with this?" Dean's blown and lustful pupils give Sam the only answer he needs.

"Just give it to me rough, none of this pansy 'don't want to hurt you' crap. Might be my first time with a guy, but I've had sex before." Dean growls, giving Sam the only 'go ahead' he needs. Sam pulls his hips to where he is almost out completely, and snaps quickly back in. Dean gives a startled gasp. But isn't in any real pain.

"Thought you wanted it rough?" Sam taunts as he pulls back again, picking up the speed. Dean's face contorts in pleasure, and it isn't long before Dean comes again.Sam thrusts a little faster until he shudders and lets go. 

The boys crumble next to each other and are soon lying comfortably in each other's arms. 

"We should do this again, soon." Sam whispers to Dean. 

"Sure, sure. As long as we finish this case before Valentine's day." Dean chuffs, and gives Sam's forehead a kiss. "Just go to sleep little brother, plenty of time to figure out how 'this' is going to work, tomorrow."


End file.
